Triacetoxyperiodinane → 1-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile

HRID 244441ノート

反応式

HRID 244441 の反応式
[CH2:1]([N:4]1[CH:8]=[C:7]([CH:9]([OH:14])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]1[C:15]#[N:16])[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:4]1[CH:8]=[C:7]([C:9](=[O:14])[C:10]([F:13])([F:11])[F:12])[CH:6]=[C:5]1[C:15]#[N:16])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 594372371-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile

生成物 1

HCID 594372991-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a room temperature solution of 1-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile (1.6 g, 7 mmol, 1 equiv.) in 50 mL of CH2Cl2 was added Dess-Martin periodinane (3.6 g, 8.3 mmol, 1.2 equiv). After 3 hours, the reaction was diluted with CH2Cl2 and made basic with saturated NaHCO3. The organic layer was separated and the aqueous extracted with CH2Cl2. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc-hexanes (0-15% gradient) to provide 1-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile which was used without further purification.

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous extracted with CH2Cl2
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-d4b6632dc2bf46299091ac700277130b
出典データセット
uspto-grants-2014_02
特許番号
US08658637B2

反応ノート

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